Vol. 25 No. 2 (2026): Mapana Journal of Sciences
Research Articles

Experimental and Computational Studies on Photophysical Properties of 1-(3-lodophenoxy methyl)-Benzo[f]Chromen-3-one by Solvatoch romic Approaches

PDF
  • Alageri Lingappa,
  • Shivaleela Basavaraj,
  • Manjula K.,
  • J. Thipperudrappa,
  • S. M. Hanagodimath
Alageri Lingappa
Department of Physics, Gulbarga University, Kalaburagi, Karnataka, India
Shivaleela Basavaraj
Department of Physics, Gulbarga University, Kalaburagi, Karnataka, India
Manjula K.
Department of Physics, Gulbarga University, Kalaburagi, Karnataka, India
J. Thipperudrappa
Department of Physics, Vijayanagara Sri Krishnadevaraya University, Ballari, Karnataka, India
S. M. Hanagodimath
Department of Physics, Gulbarga University, Kalaburagi, Karnataka, India
DOI: https://doi.org/10.12723/mjs.77.3

Published 2026-06-13

Keywords

  • DFT structure,
  • LUMO and HOMO,
  • absorption spectra,
  • fluorescence spectra,
  • EPS,
  • dipole moments
    • ...More
    Less

Copyright (c) 2026

Creative Commons License

This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.

Abstract

The iodinated derivative 13IBC3 was synthesized and its photophysical properties were studied in polar and nonpolar solvents. The ground- and excited-state dipole moments were estimated using equations. Results showed a bathochromic shift with increasing solvent polarity, indicating a larger excited-state dipole moment (μe > μg). The change in dipole moment (Δμ) was 6.92D (DFT method) and 7.12D (Semiempirical method). The Kamlet and Catalan multiple linear regression analysis revealed that solvent dielectric constants and polarizability significantly influence spectral characteristics. The excited state exhibits intramolecular charge-transfer (ICT) character. Polar solvents alter the fluorescence properties of coumarin.  The computational study was carried out with the Gaussian 16W program using the B3LYP. UV-visible spectra of solvated species were calculated using TD-DFT, which confirmed the experimental findings and provided insights into HOMO-LUMO energies, ESP maps, and nonlinear optical properties. The change in dipole moment matched the experimental value.

PDF

References

  1. . Asnaashari M, Kenari RE, Taghdisi SM, Abnous K, Farahman dfar R (2024) A novel fluorescent DNA sensor for acrylamide detection in food samples based on Single-Stranded DNA and gelred. J Fluoresc 34:2845–2860, https://doi.org/10.1007/s10895- 023-03479-7.
  2. . Erdemir GY, Topkaya D (2024) Synthesis, characterizat
  3. ion and evaluating photochemical properties of Porphyrin
  4. -substituted Azobenzene structure. J Fluoresc 34:275–281. https://doi.org/10.1007/s10895-023-03256-6.
  5. . Essam ZM, Ozmen GE, Setiawan D, Hamid RR, Abd El-Aal RM, Aneja R, Hamelberg D, Henary M (2021) Donor acceptor fluorophores: synthesis, optiproperties, TD-DFT and cytotoxicity studies. Org Biomol Chem 19:1831846.
  6. https://doi.org/10.1039/d0ob02313b
  7. . H.R. Deepa, S. Chandrasekhar, J. Thipperudrappa, Chem. Phys. Impact4(2022), 100075.
  8. . Poronik YM, Baryshnikov GV, Deperasinska I, Espinoza EM, Clark JA, Ågren H, Gryko DT, Vullev VI (2020) Deciphering the unusual fluorescence in weakly coupled bis-nitro-pyrrolo[3,2- ] pyrroles. Communications Chemistry 3. https://doi.org/ARTN.19010.1038/s42004-020-00434-6
  9. . S. Chandrasekhar, H.R. Deepa, R.M. Melavanki, S. Mogurampelly, M.M.Basanagouda, J.Thipperudrappa, S. Yallappa, Chem. Data Collect.29(2020),100516.
  10. . S. Chandrasekhar, H.R. Deepa, R. Melavanki, M.M. Basanagouda, S. Mogurampelly, J. Thipperudrappa, Luminescence.36(2021)769–787
  11. . Prajakta S. Kadolkar, Shivaraj A. Patil, Wari, Sanjeev R. Inamdar j.molliq.2020.113452.
  12. . N.N. Hamdi, M.M. Chebli, H. Grib, M. Brahimi, A.M.S. Silva, Synthesis DFT/TD- DFT theoretical studies and experimental solvatochromic shift methods on determination of ground and excited state dipole moments of 3- (2- hydroxybenzoyl) coumarins, J. Mol. Struct. 1175 (2019) 811–820, https://doi.org/ 10.1016/j.
  13. molstruc.2018.08.039.
  14. . L.C. Luz, M.G. Gündüz, R. Beal, G.M. Zanotto, E.R. Kuhn, P.A. Netz, C. S¸ afak, P.F.B. Gonçalves, Fabiano da silveira santos, fabiano severo rodembusch, J Photochem. Photobiol. 429 (2022),113915.
  15. . Mallikarjun, K. Patil, M.G. Kotresh, Sanjeev R. Inamdar, https://doi.org/10.1016/j.saa.2019.02.022
  16. . Shivaraj A. Patil, Prajakta S. Kadolkar, Manjunath, N. Wari, Sanjeev, R. Inamdar, S2352492821007248.
  17. . J. Thipperudrappa, D.S. Biradar, M.T. Lagare, S.M. Hanagodimath, S.R. Inmdar, S J.S. Kadadevaramath, https://doi.org/10.1016/j.jphotochem.2005.05.016
  18. . K. Vibha a, N.C. Prachalith a , R. Annoji Reddy a,b , M.N. Ravikantha a,c , J. Thipperudrappa a, [15]. M. K. Patil, M.G. Kotresh, S.R. Inamdar, Spectrochimica ActaPart A, DOI: S1386–1425(19)30134–9. https://doi.org/10.1016/j.
  19. saa.2019.02.022.
  20. . N. Sunil Kumar a , K.N.N. Prasad b,* , S. Chandras
  21. ekhar b , J. Thipperudrappa c, sciencedirectassets.com, https://doi.org/10.1016/j.chphi.2022.100136
  22. . Jing Han W, Chih-Ling C, Zhe Wei Z, Mahdy EL, Ahmed FM (2022) Facile metal-free synthesis of pyrrolo
  23. ,2-b]pyrrolyl based conjugated microporous polymers for high-performance photocatalytic degradation of organic pollutants. Polym Chem 13:37:5300–5308.https://
  24. doi.org/10.1039 /d2py00658h
  25. . Bhardwaj K, Anand T, Jangir R, Sahoo SK (2024) Aggregation Induced emission active Benzidine-Pyridoxal derived scaffold for detecting Fe(3+) and pH. J Fluoresc 34:2917–2926. https://doi.org/10.1007/s10895-023-03503-w.
  26. . HA.Z. Sabek, AM.M. Alazaly, D. Salah, HS. Abdel-Samad, MA. Ismail,A.A. Abdel- Shafi, RSC Adv. 10 (2020) 43459–43471.
  27. . S.N. Saravanamoorthy, G. Sathiyapriya, M. Sivasakthi, Int. J. Res. Appl. Sci. Eng. Technol. 7 (2019) 1017–1028 (IJRASET).
  28. . Mahesh, S. Najare , Mallikarjun K. Patil, Afra Quasar A. Nadaf , Shivaraj Mantur, Manjunatha Garbhagudi, Supreet Gaonkar , Sanjeev R. Inamdar , Imtiyaz Ahmed M. Khazi j.molstruc.2019.127032.pdf
  29. . S.K. Patila, M.N. Warib, C. Yohannan Panickerc, Inamdar, j.saa.2013.12.031.pdf
  30. . Airin Antony, J.Mitra, Refractive index-assisted UV/Vis spectrophotometry to overcome spectral interference by https://www.sciencedirect.com/science/article/abs/pii/S0003267020312691,
  31. . A. Frisch, R. Dennington, T. Keith, J. Millam, A. Nielsen, A.J. Holder, Hiscocks, Gauss View Version 5 User Manual, Gaussian Inc, Wallingford,CT,USA,2009.
  32. . N. Muruganantham, R. Sivakumar, N. Anbalagan, V.Gunasekaran, J. Thipperudrappa, Leonard,Biol. Pharm. Bull. 27 (2004) 1683–1687 [25].
  33. Y.F. Nadaf, B.G. Mulimani, M. Gopal,. Inamdar, j.theochem.2004.01.049.pdf
  34. . Hawks AM, Altman D, Faddis R, Wagner EM, Bell KJ, Charland Martin A, Collier GS (2023) Relating design and optoelectronic properties of 1,4-Dihydropyrrolo [3,2-b] pyrroles bearing biphenyl substituents. J Phys Chem B
  35. :7352–7360. https://doi.org/10.1021/acs.jpcb.3c03061.
  36. . Hawks AM, Daniel LM, Sorto VS, Mauro J, Skiouris P, Collier GS (2024) Expanding color control of anodically coloring electrochromes based on Electron-Rich 1,4-Dihydropyrrolo [3,2-b] pyrroles. ACS Appl Opt Mater 2:1235– 1244. https://doi.org/10.1021/acsaom.4c00197
  37. . Radha Goudar, Ritu Gupta, Giridhar U. Kulkarni, Sanjeev R. Inamdar, J. Fluoresc.25(2015) 1671–1679, https://doi.org/10.1007/s10895-015-1654-6.
  38. . V.V. Koppal, Raveendra Melavanki, Raviraj Kusanur, N.R. Patil, Analysis of Fluorescence Quenching of Coumarin Derivative under Steady State and Transient State Methods, https://doi.org/10.1007/s10895-020-02663-3
  39. . S.P. Olivares, S.Risso, M.I. Gutie´rrez, Spectrochim. ActaA71(2008)336–339
  40. . J.A. Dean, Lange’sHandbookofChemistry,15thed., McGraw-Hill, New York, 1999
  41. . X. Zhang, A.S. Shetty, S.A. Jenekhe, Macromolecules
  42. (1999)7422–7429
  43. . J.R. Lackowicz, Principles of Fluorescence Spectroscopy, Plenum Press, New York,1983.z
  44. . M.J. Kamlet, J.L.M. Abboud, M.H. Abraham, R.W. Taft, J. Org. Chem. 48 (1983)2877–2887.
  45. . M.J. Kamlet, Prog. Phys.Org.Chem.13(1982)485.
  46. . R.B. da Silva, F. Lange Coelho, F.S. Rodembusch, R.S. Schwab, J.M.F.M. Schneider,D. da Silveira Rampon, P.H. Schneider, New J. Chem. 43 (2019) 11596–11603.
  47. . Sanjeev, R. Inamdar, James, R. Mannekutla, M.S. Sannaikar, M.N.Wari, B.G. Mulimani, M.I. Savadatti, https:
  48. //doi.org/10.1016/j.molliq.2018.07.005
  49. . G.H. Pujar, M.N. Wari, B. Steffi, H. Varsha, B. Kavita, C. Yohannan Panicker, http://dx.doi.org/10.1016/j.molliq.
  50. 08.078
  51. . Jana Basavaraja, S.R. Inamdar, H.M. Suresh Kumar j.saa.2016.07.010.pdf
  52. . M.J.Kamlet,J.L.Abboud,R.W.Taft,J.Am.Chem.Soc.99 (1977)6027–6038

Most read articles by the same author(s)